# Evidence: hydrogen-bond basicity

Parent: — · class: molecular interaction · names merged here: hydrogen bond acceptor strength; hydrogen-bond acceptor basicity; hydrogen-bond acceptor strength; hydrogen-bond basicity; hydrogen-bond donor and acceptor strength

5 papers measured or used it, 0 only mentioned it (of 207 kept papers). Papers in year order; each section heading ends with the paper's category / subcategory. Generated by tools/build_evidence.py from registry/concepts.csv and the cards; do not edit.

## 1997 Taylor — Spectroscopic Characterization of Interactions Between PVP and Indomethacin in Amorphous Molecular Dispersions · Solid state stability / Miscibility and drug-polymer interactions

[1997-taylor-pvp-indomethacin-amorphous-molecular-dispersions](../../../cards/1997-taylor-pvp-indomethacin-amorphous-molecular-dispersions/paper.html) · Solid state stability / Miscibility and drug-polymer interactions · used · as: hydrogen-bond acceptor basicity

| id | kind | content | locator |
|---|---|---|---|
| C36 | claim, mechanism, authors: "would explain" | The more basic nature of the PVP amide group compared with the carboxylic acid group would explain PVP's ability to disrupt the dimers [rests on: cited: ref 33] | p.1696 |

## 2011 Kestur — Influence of polymer chemistry on crystal growth inhibition of two chemically diverse organic molecules · Solid state stability / Miscibility and drug-polymer interactions

[2011-kestur-polymer-chemistry-crystal-growth-bifonazole-nimesulide](../../../cards/2011-kestur-polymer-chemistry-crystal-growth-bifonazole-nimesulide/paper.html) · Solid state stability / Miscibility and drug-polymer interactions · used · as: hydrogen bond acceptor strength

| id | kind | content | locator |
|---|---|---|---|
| C16 | claim, mechanism, authors: "would be expected"; "should disrupt" | The bifonazole imidazole nitrogen should be a better acceptor than the PAA carbonyl and so disrupt PAA self-association [rests on: R22] | p.6716 |
| C26 | claim, mechanism, authors: "may be related" | The somewhat better performance of PVP and PVP/VA than PVAc may be related to their stronger acceptor [rests on: R9, R14, R15, R16; cited: ref 27] | p.6717 |

## 2011 Eerdenbrugh — An ab initio polymer selection methodology to prevent crystallization in amorphous solid dispersions by application of crystal engineering principles · Solid state stability / Miscibility and drug-polymer interactions

[2011-van-eerdenbrugh-ab-initio-polymer-selection-asd-crystallization](../../../cards/2011-van-eerdenbrugh-ab-initio-polymer-selection-asd-crystallization/paper.html) · Solid state stability / Miscibility and drug-polymer interactions · used · as: hydrogen-bond donor and acceptor strength

| id | kind | content | locator |
|---|---|---|---|
| R1 | record, simulated (pKa, P7); derived (intramolecular, donor and acceptor classes, P8); cited (pKBHX values, ref 26) | hydrogen-bonding characteristics of the drug functional groups — 15 model drugs (M1–M15) — sub-table below; mmol g−1 printed once per drug (blank cells for further groups); footnote g: basic function (B + H+ → BH+); footnote a: classes Weak <0.75 < Medium < 1.5 < Strong < 2.25 < Very Strong, used as only pKBHX values below 3 (not up to 5.5) occurred; footnote b: no pKBHX values for COOH acceptors, carbonyl taken as comparable to an ester | Table 1, p.6173 |
| R2 | record, simulated (pKa, P7); derived (donor and acceptor classes, P8); cited (pKBHX values) | hydrogen-bonding characteristics of the polymer functional groups — 7 polymers (M16–M22) — sub-table below; footnote b: basic function (B + H+ → BH+); footnote c: no values for COOH acceptors, carbonyl taken as comparable to an ester; footnotes a and c cite ref 18 (X2) | Table 2, p.6174 |
| C13 | claim, assumption, authors: "regarded" | Donor strength follows the electronegativity of the bonding atom (F–H > O–H > N–H > C–H); O–H donors are regarded as strong, N–H as medium, a carboxylic acid O–H as very strong, and some N–H donors as strong to very strong from crystal structures, pKa values and substituents [rests on: cited: ref 25; R1] | p.6172 |
| C14 | claim, assumption, authors: asserted; "regarded" | Acceptor strength is read from the pKBHX scale, a thermodynamic basicity scale from association constants of 1:1 complexes with 4-fluorophenol that covers many drug-like structures; a COOH carbonyl is regarded as comparable to an ester [rests on: cited: ref 26; R1, R2] | p.6172-6173; Tables 1-2 footnotes |

## 2013 Wegiel — Mid-infrared spectroscopy as a polymer selection tool for formulating amorphous solid dispersions · Solid state stability / Miscibility and drug-polymer interactions

[2013-wegiel-mid-ir-polymer-selection-polyphenol-asd-stability](../../../cards/2013-wegiel-mid-ir-polymer-selection-polyphenol-asd-stability/paper.html) · Solid state stability / Miscibility and drug-polymer interactions · used · as: hydrogen-bond acceptor strength

| id | kind | content | locator |
|---|---|---|---|
| R12 | record, derived (group content; calculation not printed) and cited (pKBHX values, ref 39) | hydrogen-bond donor and acceptor groups of the polymers — P8; donor (D) and acceptor (A) marks as printed — sub-table below | Table 4, p.8 |
| P8 | method | polymer hydrogen-bond donor and acceptor analysis | p.8-9 |
| C29 | claim, assumption, authors: asserted | The Van Eerdenbrugh approach behind Table 4 applies standard hydrogen-bond rules (all good donors and acceptors are used; six-membered intramolecular rings form more readily than intermolecular bonds; the best donors and acceptors left after intramolecular bonding pair with each other) and classifies acceptor strength on the pKBHX scale [rests on: cited: refs 28, 37-39] | p.8-9 |
| C31 | claim, generalisation, authors: "it is expected"; "are not expected" | The best hydrogen bonds are expected with the strongest acceptors (PVP amide very strong, E100 tertiary amine strong, the other polymers medium with pKBHX about 1); polymers with strong donor groups (PAA, CMCAB) are not expected to be effective inhibitors because the flavonoids' one strong acceptor is held in an intramolecular bond [rests on: R12] | p.9 |

## 2013 Wegiel — Crystallization of Amorphous Solid Dispersions of Resveratrol during Preparation and Storage—Impact of Different Polymers · Solid state stability / Physical stability

[2013-wegiel-resveratrol-asd-polymer-crystallization-stability](../../../cards/2013-wegiel-resveratrol-asd-polymer-crystallization-stability/paper.html) · Solid state stability / Physical stability · used · as: hydrogen-bond basicity

| id | kind | content | locator |
|---|---|---|---|
| R17 | record, cited (pKBHX values, ref 38); derived (group content in mmol/g, relation not printed; strength classes by E2) | hydrogen-bond donor and acceptor groups of the polymers — per repeat-unit chemistry (Fig. 1) — sub-table below | Table 4, p.182 |
| E2 | equation | hydrogen-bond acceptor strength classes on the pKBHX scale: Weak < 0.75 < Medium < 1.5 < Strong < 2.25 < Very Strong | Table 4 footnote a, p.182; text p.181 |
| P10 | method | hydrogen-bond donor and acceptor ranking (pKBHX scale) | p.181-182 |
| C30 | claim, assumption, authors: asserted | Donor and acceptor groups can be categorized with Etter's hydrogen-bond rules as applied by Van Eerdenbrugh and Taylor and with the pKBHX acceptor scale; the only donors are OH groups, resveratrol phenolic OH is a stronger donor than the aliphatic OH of the cellulose polymers, PAA carboxyls are the strongest polymer donors, and resveratrol is a weak acceptor [rests on: R17; cited: refs 23, 36-38] | p.181-182 |